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Synthesis and spectroscopic properties of ?,?'-dibenzo-3,5,8-triaryl-BODIPYs.

ABSTRACT: A series of ?,?'-bicyclo-3,5-diaryl-BODIPYs were synthesized from the corresponding ?,?'-bicyclo-3,5-diiodo-BODIPYs (1a,b) via Pd(0)-mediated Suzuki cross-coupling reactions in 82-92% yields. Subsequent aromatization with DDQ afforded the corresponding ?,?'-dibenzo-aryl-BODIPYs, which showed red-shifted absorptions and emissions in the near-IR range. The dibenzo-appended BODIPYs showed characteristic 1H-, 13C-, 11B- and 19F-NMR shifts, and nearly planar conformations by X-ray crystallography.

SUBMITTER: Meng Q

PROVIDER: S-EPMC5047295 | biostudies-literature | 2016

REPOSITORIES: biostudies-literature

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Synthesis and spectroscopic properties of β,β'-dibenzo-3,5,8-triaryl-BODIPYs.

Meng Qianli Q Fronczek Frank R FR Vicente M Graça H MG

New journal of chemistry = Nouveau journal de chimie 20160208 7

A series of β,β'-bicyclo-3,5-diaryl-BODIPYs were synthesized from the corresponding β,β'-bicyclo-3,5-diiodo-BODIPYs (1a,b) via Pd(0)-mediated Suzuki cross-coupling reactions in 82-92% yields. Subsequent aromatization with DDQ afforded the corresponding β,β'-dibenzo-aryl-BODIPYs, which showed red-shifted absorptions and emissions in the near-IR range. The dibenzo-appended BODIPYs showed characteristic 1H-, 13C-, 11B- and 19F-NMR shifts, an ...[more]

PMID: 27708532

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